Heterocyclic chromenes and their use in the field of ophthalmic optics

Abstract

The invention relates to photochromic compounds of general formula: ##STR1## wherein R.sup.a, R.sup.b and R.sup.c is denote hydrogen; alkyl; aryl; OR, SR, COR or COOR, in which R denotes hydrogen, alkyl or aryl, amino of formula NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 denote hydrogen, alkyl, cycloalkyl or an aryl; a halogen atom; a mono- or polyhaloalkyl group; or an NO.sub.2, CN or SCN group; n and m denote integers from 1 to 5; p is equal to 1 or 2; and H is a 5-members aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen and sulfur, these heterocyclic nuclei being eventually substituted by one or more alkyl, alkoxy, amino, aryl or aralkyl groups or condensed with a phenyl nucleus, a substituted phenyl nucleus or a 6-members cycloaliphatic nucleus and to their use in ophtalmic optics.

Claims

1. A photochromic compound which is of the original formula: ##STR16## wherein R.sup.a, R.sup.b and R.sup.c are independently of each other, a hydrogen atom, an alkyl group, an aryl group, an OR, SR, COR or COOR group, where R denotes a hydrogen atom, an alkyl group or an aryl group, an amino group of formula NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 denote, independently of each other, a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group; a halogen atom; a mono- or polyhaloalkyl group; or an NO.sub.2, CN or SON group; n and m denote integers from 1 to 5; p is equal to 1 or 2; R.sup.a, R.sup.b and R.sup.c may have different meanings when m, n and p are greater than 1; and H is a 5-members aromatic heterocycle of the general formula: ##STR17## in which: X or Z represents --N-- or --NH--, and the remaining one of X or Z represents S, O or a CR.sub.8 radical in which R.sub.8 is hydrogen, C.sub.1 --C.sub.6 alkyl or phenyl, the carbon atom being linked to the neighboring atom by a double bond; and

R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl or when X or Z is --NH--, may form with the remaining one of X or Z a phenyl ring, or a substituted phenyl ring.

2. The compound of claim 1 comprising compounds of a formula: ##STR18##

3. An ophthalmic lens comprising a transparent organic polymer material and at least one photochromic compound as defined in claim 1, in an amount sufficient to enable a said ophthalmic lens to change color upon exposure to ultraviolet radiation.

4. The ophthalmic lens of claim 3, wherein said at least one photochromic compound is in the form of a coating on said transparent organic polymer material.

5. The ophthalmic lens of claim 3, wherein said at least one photochromic compound is incorporated within said transparent organic polymer material.

6. The ophthalmic lens of claim 5, which contains 0.01 to 20% by weight of photochromic compounds.

7. The ophthalmic lens of claim 5, which contains 0.05 to 10% by weight of photochromic compounds.

8. The ophthalmic lens of claim 3, wherein said transparent organic polymer material is selected from the group consisting of polyol(allylcarbonate), polyacrylate, poly(alkylacrylate) polymers, cellulose acetate, cellulose triacetate, cellulose propionate acetate, cellulose butyrate acetate, poly(vinylacetate), poly(vinyl alcohol), polyurethanes, polycarbonates, poly(ethylene terephthalates), polystyrenes, poly(styrene methylmethacrylates), styrene and acrylonitrile copolymers, and polyvinylbutyrates.